Patrick Dempsey is, according to our highly unscientific estimation, the world’s most famous impossibly good-looking race-car-driving actor. Dempsey began his racing career (sort of) back in high school, in Maine, on the ski slopes, where he picked up a state championship in the slalom. Since then, in addition to an on-screen career that has avoided the pitfalls of most 80s child stars, Dempsey has raced on some of the most celebrated courses in the sport. These include the 24 Hours at LeMans, the 24 Hours at Daytona, and something oxymoronically called American LeMans.

Since we love handsome actors and fast cars—and find the combination essentially irresistible—we gave Patrick a call to discuss cursed Ferraris, frozen Mercedes, wrecked Porsches, and the unerring coolness of Paul Newman. Highlights from our conversation are below.

Brett Berk: Aside from your acting, and your deliciously luxuriant hair, you’re probably known best as a race-car driver. Being an automotive writer, I’ve received varied reports of your racing Aston-Martins, Mazdas, and now Maseratis. Are any or all of these true?

Patrick Dempsey: That’s true. This year I did the Maserati race at Sonoma, which was a lot of fun, and the first time I had a chance to race up there. I’ve been racing Mazda RX-8s in the Rolex Series for about five years now. Aston-Martins in the Continental series this year. A Ferrari at LeMans. And BC Dune Buggies in the Baja 1000 Rally.
In addition to these, I’m sure you own some non-race cars, right? Let’s go through a few scenarios and you can tell me which car from your collection you’d drive, and why. We’ll start with a leisurely drive up the coast on a day off from work.

You can’t go wrong with my 1963 Porsche 356. A 356 convertible is a perfect California car. It’s iconic. It’s easy and reliable to drive. And it’s bulletproof.
Taking one of the kids to an activity?

With the family, I would take the 280 SE—the Mercedes sedan convertible. Put the top down and just cruise.
Date night with your wife?

I’d take the Jag. I have a 1972 E-Type V-12, another iconic car. If you have them well sorted, they’re quite fast and can really handle well. And it’s extremely smooth.
Driving to work at the studio?

My daily driver now is a Mercedes SLS Gullwing, in silver, which is a quintessentially German color. The SLS is a perfect around-town car because if just want to cruise along, do your business, you can do that. And then if you want to get sporty, it’s a monster. You can really be aggressive in that car.
Do you have a “unicorn”—a fantasy car you’d really love to own?

I would like an original Gullwing. But I think the car to get would be the original Mercedes SL Roadster—the 300 SL. That would be the perfect car. I’ve always just been connected to it—there’s an elegance, a sophistication to it. And then, if you’re looking at Italian cars, certainly the Maseratis of the 50s are really beautiful cars as well.
What is the worst car you’ve ever owned? And you can define “worst” in whatever way you want.

I had a Ferrari Daytona, which was a beast to drive. I mean, once it was up and running, it was great, but it didn’t drive easily—there was no power steering; it was a big V-12. It was beautiful to look at—sculpturally, it’s just fantastic—but on a practical level, it wasn’t something you could use as a daily driver. But that might sound nitpicky, right?
Um . . . maybe? “The worst car I ever owned was a Ferrari Daytona.”

[Laughs.] I’ve been very fortunate. The only other car I can think of that gave me trouble was my first car, which was a diesel Mercedes. In the wintertime, I could never keep that thing going—I was back East in Maine at the time, and if I didn’t plug it in at night [to warm the engine block], I could never get it started.
For our last question, we ask all of our Stars and Cars participants to tell us about the most embarrassing thing that’s ever happened to them in a car.

Early on when I bought the Porsche 356—this was 20, 25 years ago—I was backing out from my place in a hurry. Where I was living at the time, the alleyway to get out was very narrow and I had to back out to get out of it. And while I was turned around looking behind me, making sure I wasn’t going to back into anything, I heard the door just getting ripped off the side of the car. I had forgotten to close the door before I started driving. And that was terrible, a terrible sound. I could never get the door to close properly after that. I had to kick it closed, and then tie it up with, like, a bungee cord. That was pretty embarrassing.
Yeah, that’s not exactly the way you want to be seen driving around in a vintage Porsche. Though Paul Newman had a really crappy Porsche 356 in that movie Harper, and he still managed to look consistently cool.